# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_b210926a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213700'
loop_
_audit_author_name
_audit_author_address
'Xian Luo'
;Soochow University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Br2 F6 N2 O3'
_chemical_formula_sum            'C16 H14 Br2 F6 N2 O3'
_chemical_formula_weight         556.11
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.5935(8)
_cell_length_b                   10.4364(9)
_cell_length_c                   10.8779(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.610(3)
_cell_angle_gamma                90
_cell_volume                     972.43(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8031
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.728
_shelx_estimated_absorpt_T_min   0.417
_exptl_absorpt_coefficient_mu    4.245
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1638 before and 0.1033 after correction.
The Ratio of minimum to maximum transmission is 0.4492.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14095
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.709
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3460
_reflns_number_total             4345
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.129(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C14(H14)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.76580(7) 0.71827(8) 0.14812(6) 0.0490(2) Uani 1 1 d . . . . .
Br2 Br 0.82422(10) 0.40107(7) 0.57339(8) 0.0550(3) Uani 1 1 d . . . . .
O3 O 0.3613(5) 0.7830(4) 0.5817(4) 0.0328(10) Uani 1 1 d . . . . .
F1 F 0.1743(6) 0.9803(5) 0.5070(6) 0.0721(15) Uani 1 1 d . . . . .
F3 F 0.0544(6) 0.8758(6) 0.3630(5) 0.0724(15) Uani 1 1 d . . . . .
O2 O 0.8182(7) 0.7864(5) 0.8511(5) 0.0451(13) Uani 1 1 d . . . . .
O1 O 0.8938(6) 1.0145(6) 0.7707(5) 0.0522(14) Uani 1 1 d . . . . .
F5 F 0.3489(6) 0.5672(5) 0.4266(7) 0.082(2) Uani 1 1 d . . . . .
F2 F 0.0301(6) 0.8223(6) 0.5468(6) 0.0719(15) Uani 1 1 d . . . . .
N1 N 0.7415(7) 0.8387(6) 0.7430(5) 0.0355(13) Uani 1 1 d . . . . .
F6 F 0.1276(7) 0.6270(7) 0.3448(7) 0.091(2) Uani 1 1 d . . . . .
F4 F 0.1565(8) 0.5886(5) 0.5377(7) 0.088(2) Uani 1 1 d . . . . .
N2 N 0.6296(7) 0.6384(5) 0.6771(5) 0.0344(12) Uani 1 1 d . . . . .
H2 H 0.626987 0.572124 0.723878 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6390(8) 0.7749(6) 0.3743(6) 0.0298(14) Uani 1 1 d . . . . .
H16 H 0.603183 0.849626 0.335051 0.036 Uiso 1 1 calc R U . . .
C15 C 0.7207(8) 0.6835(7) 0.3130(6) 0.0331(14) Uani 1 1 d . . . . .
C14 C 0.7733(8) 0.5720(7) 0.3688(7) 0.0367(16) Uani 1 1 d . . . . .
H14 H 0.826195 0.511979 0.324717 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7475(8) 0.5492(6) 0.4904(7) 0.0347(14) Uani 1 1 d . . . . .
C3 C 0.2739(8) 0.7770(7) 0.4680(7) 0.0330(15) Uani 1 1 d . . . . .
H3 H 0.337537 0.805841 0.402496 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6687(7) 0.6403(6) 0.5562(6) 0.0298(13) Uani 1 1 d . . . . .
C4 C 0.5235(8) 0.8258(6) 0.5856(6) 0.0286(13) Uani 1 1 d . . . . .
C7 C 0.7855(8) 0.9593(7) 0.7146(6) 0.0383(16) Uani 1 1 d . . . . .
C6 C 0.6961(9) 1.0162(7) 0.6027(7) 0.0404(16) Uani 1 1 d . . . . .
H6A H 0.752240 0.997291 0.530955 0.048 Uiso 1 1 calc R U . . .
H6B H 0.694671 1.108617 0.612216 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5294(8) 0.9699(6) 0.5779(6) 0.0350(15) Uani 1 1 d . . . . .
H5A H 0.464993 1.006910 0.637969 0.042 Uiso 1 1 calc R U . . .
H5B H 0.488495 0.997601 0.496510 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5936(8) 0.7700(6) 0.7107(6) 0.0323(14) Uani 1 1 d . . . . .
C11 C 0.6127(8) 0.7510(6) 0.4959(6) 0.0278(13) Uani 1 1 d . . . . .
C10 C 0.9664(11) 0.7347(10) 0.8273(10) 0.058(2) Uani 1 1 d . . . . .
H10A H 0.952876 0.672221 0.762561 0.088 Uiso 1 1 calc R U . . .
H10B H 1.013204 0.694873 0.900705 0.088 Uiso 1 1 calc R U . . .
H10C H 1.032806 0.802377 0.802485 0.088 Uiso 1 1 calc R U . . .
C9 C 0.4899(9) 0.7759(8) 0.8164(7) 0.0420(17) Uani 1 1 d . . . . .
H9A H 0.546732 0.745878 0.890448 0.063 Uiso 1 1 calc R U . . .
H9B H 0.399821 0.722707 0.798100 0.063 Uiso 1 1 calc R U . . .
H9C H 0.457194 0.862716 0.827906 0.063 Uiso 1 1 calc R U . . .
C1 C 0.1302(9) 0.8652(9) 0.4732(8) 0.0461(18) Uani 1 1 d . . . . .
C2 C 0.2262(10) 0.6398(9) 0.4461(9) 0.056(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.900(7) . ?
Br2 C13 1.883(7) . ?
O3 C3 1.396(9) . ?
O3 C4 1.462(8) . ?
F1 C1 1.304(10) . ?
F3 C1 1.322(10) . ?
O2 N1 1.411(8) . ?
O2 C10 1.425(11) . ?
O1 C7 1.216(8) . ?
F5 C2 1.330(10) . ?
F2 C1 1.301(10) . ?
N1 C7 1.358(10) . ?
N1 C8 1.476(9) . ?
F6 C2 1.342(11) . ?
F4 C2 1.317(12) . ?
N2 H2 0.8600 . ?
N2 C12 1.384(9) . ?
N2 C8 1.460(9) . ?
C16 H16 0.9300 . ?
C16 C15 1.387(10) . ?
C16 C11 1.382(10) . ?
C15 C14 1.371(10) . ?
C14 H14 0.9300 . ?
C14 C13 1.379(11) . ?
C13 C12 1.397(10) . ?
C3 H3 0.9800 . ?
C3 C1 1.544(11) . ?
C3 C2 1.503(12) . ?
C12 C11 1.395(9) . ?
C4 C5 1.507(10) . ?
C4 C8 1.556(9) . ?
C4 C11 1.507(9) . ?
C7 C6 1.508(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.515(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 C9 1.513(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 C4 118.9(5) . . ?
N1 O2 C10 111.0(6) . . ?
O2 N1 C8 110.3(5) . . ?
C7 N1 O2 115.4(6) . . ?
C7 N1 C8 130.2(6) . . ?
C12 N2 H2 126.4 . . ?
C12 N2 C8 107.3(5) . . ?
C8 N2 H2 126.4 . . ?
C15 C16 H16 121.2 . . ?
C11 C16 H16 121.2 . . ?
C11 C16 C15 117.6(6) . . ?
C16 C15 Br1 118.2(5) . . ?
C14 C15 Br1 119.7(5) . . ?
C14 C15 C16 122.1(6) . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C14 C13 Br2 121.6(5) . . ?
C14 C13 C12 119.7(6) . . ?
C12 C13 Br2 118.6(5) . . ?
O3 C3 H3 109.8 . . ?
O3 C3 C1 108.4(6) . . ?
O3 C3 C2 107.6(6) . . ?
C1 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C2 C3 C1 111.4(6) . . ?
N2 C12 C13 130.0(6) . . ?
N2 C12 C11 111.0(6) . . ?
C11 C12 C13 119.1(6) . . ?
O3 C4 C5 109.9(5) . . ?
O3 C4 C8 102.2(5) . . ?
O3 C4 C11 110.9(5) . . ?
C5 C4 C8 114.2(5) . . ?
C11 C4 C5 117.4(5) . . ?
C11 C4 C8 101.0(5) . . ?
O1 C7 N1 122.7(7) . . ?
O1 C7 C6 122.6(7) . . ?
N1 C7 C6 114.6(6) . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C7 C6 C5 115.5(6) . . ?
H6A C6 H6B 107.5 . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C4 C5 C6 110.1(6) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
N1 C8 C4 107.0(5) . . ?
N1 C8 C9 110.3(6) . . ?
N2 C8 N1 108.7(6) . . ?
N2 C8 C4 102.0(5) . . ?
N2 C8 C9 112.2(6) . . ?
C9 C8 C4 116.1(6) . . ?
C16 C11 C12 121.5(6) . . ?
C16 C11 C4 131.0(6) . . ?
C12 C11 C4 107.4(6) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F1 C1 F3 106.8(7) . . ?
F1 C1 C3 110.1(6) . . ?
F3 C1 C3 110.7(7) . . ?
F2 C1 F1 109.6(7) . . ?
F2 C1 F3 106.5(7) . . ?
F2 C1 C3 112.8(7) . . ?
F5 C2 F6 105.6(7) . . ?
F5 C2 C3 111.0(7) . . ?
F6 C2 C3 111.8(8) . . ?
F4 C2 F5 107.7(9) . . ?
F4 C2 F6 106.6(8) . . ?
F4 C2 C3 113.7(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C15 C14 C13 176.8(5) . . . . ?
Br2 C13 C12 N2 -3.0(10) . . . . ?
Br2 C13 C12 C11 179.4(5) . . . . ?
O3 C3 C1 F1 54.0(8) . . . . ?
O3 C3 C1 F3 172.0(6) . . . . ?
O3 C3 C1 F2 -68.7(8) . . . . ?
O3 C3 C2 F5 -69.0(9) . . . . ?
O3 C3 C2 F6 173.4(7) . . . . ?
O3 C3 C2 F4 52.7(9) . . . . ?
O3 C4 C5 C6 170.8(5) . . . . ?
O3 C4 C8 N1 -163.1(5) . . . . ?
O3 C4 C8 N2 82.9(6) . . . . ?
O3 C4 C8 C9 -39.4(7) . . . . ?
O3 C4 C11 C16 91.8(8) . . . . ?
O3 C4 C11 C12 -86.5(6) . . . . ?
O2 N1 C7 O1 6.9(10) . . . . ?
O2 N1 C7 C6 -176.9(6) . . . . ?
O2 N1 C8 N2 -66.0(7) . . . . ?
O2 N1 C8 C4 -175.5(5) . . . . ?
O2 N1 C8 C9 57.4(7) . . . . ?
O1 C7 C6 C5 -153.9(7) . . . . ?
N1 C7 C6 C5 29.9(9) . . . . ?
N2 C12 C11 C16 179.2(6) . . . . ?
N2 C12 C11 C4 -2.2(7) . . . . ?
C16 C15 C14 C13 -1.1(11) . . . . ?
C15 C16 C11 C12 1.3(10) . . . . ?
C15 C16 C11 C4 -176.8(7) . . . . ?
C15 C14 C13 Br2 -177.5(5) . . . . ?
C15 C14 C13 C12 -0.4(11) . . . . ?
C14 C13 C12 N2 179.8(7) . . . . ?
C14 C13 C12 C11 2.2(10) . . . . ?
C13 C12 C11 C16 -2.7(10) . . . . ?
C13 C12 C11 C4 175.8(6) . . . . ?
C3 O3 C4 C5 79.4(6) . . . . ?
C3 O3 C4 C8 -159.0(5) . . . . ?
C3 O3 C4 C11 -52.0(7) . . . . ?
C12 N2 C8 N1 -80.8(6) . . . . ?
C12 N2 C8 C4 32.0(7) . . . . ?
C12 N2 C8 C9 156.9(6) . . . . ?
C4 O3 C3 C1 -121.0(6) . . . . ?
C4 O3 C3 C2 118.4(6) . . . . ?
C7 N1 C8 N2 138.3(7) . . . . ?
C7 N1 C8 C4 28.8(9) . . . . ?
C7 N1 C8 C9 -98.3(8) . . . . ?
C7 C6 C5 C4 -47.9(8) . . . . ?
C5 C4 C8 N1 -44.5(7) . . . . ?
C5 C4 C8 N2 -158.5(5) . . . . ?
C5 C4 C8 C9 79.2(7) . . . . ?
C5 C4 C11 C16 -35.6(10) . . . . ?
C5 C4 C11 C12 146.1(6) . . . . ?
C8 N1 C7 O1 161.6(7) . . . . ?
C8 N1 C7 C6 -22.2(11) . . . . ?
C8 N2 C12 C13 162.5(7) . . . . ?
C8 N2 C12 C11 -19.7(7) . . . . ?
C8 C4 C5 C6 56.6(7) . . . . ?
C8 C4 C11 C16 -160.4(7) . . . . ?
C8 C4 C11 C12 21.3(6) . . . . ?
C11 C16 C15 Br1 -177.3(5) . . . . ?
C11 C16 C15 C14 0.6(11) . . . . ?
C11 C4 C5 C6 -61.3(8) . . . . ?
C11 C4 C8 N1 82.5(6) . . . . ?
C11 C4 C8 N2 -31.6(6) . . . . ?
C11 C4 C8 C9 -153.8(6) . . . . ?
C10 O2 N1 C7 -82.2(8) . . . . ?
C10 O2 N1 C8 118.1(7) . . . . ?
C1 C3 C2 F5 172.3(8) . . . . ?
C1 C3 C2 F6 54.7(9) . . . . ?
C1 C3 C2 F4 -66.1(10) . . . . ?
C2 C3 C1 F1 172.3(7) . . . . ?
C2 C3 C1 F3 -69.8(9) . . . . ?
C2 C3 C1 F2 49.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b220530a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213712'
loop_
_audit_author_name
_audit_author_address
'Xian Luo'
;Soochow University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_audit_creation_date             2022-05-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 F N2 O2'
_chemical_formula_sum            'C18 H15 F N2 O2'
_chemical_formula_weight         310.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1831(13)
_cell_length_b                   11.7646(14)
_cell_length_c                   12.1011(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.533(3)
_cell_angle_gamma                90
_cell_volume                     1547.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4739
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.7389.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1428
_reflns_number_total             3165
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C12(H12), C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55551(17) 0.36519(16) 0.48864(17) 0.0736(6) Uani 1 1 d . . . . .
O2 O 0.46144(15) 0.26496(16) 0.65992(15) 0.0688(6) Uani 1 1 d . . . . .
N2 N 0.39380(17) 0.31214(18) 0.55992(16) 0.0535(6) Uani 1 1 d . . . . .
F1 F 0.14890(19) 0.67503(16) 0.68810(17) 0.1125(7) Uani 1 1 d . . . . .
N1 N 0.12485(19) 0.2150(2) 0.62728(18) 0.0650(6) Uani 1 1 d . . . . .
C17 C 0.4458(3) 0.3553(2) 0.4800(2) 0.0545(7) Uani 1 1 d . . . . .
C8 C 0.2609(2) 0.3085(2) 0.5357(2) 0.0550(7) Uani 1 1 d . . . . .
C9 C 0.2019(2) 0.3939(2) 0.6012(2) 0.0576(7) Uani 1 1 d . . . . .
C10 C 0.1204(2) 0.3340(2) 0.6477(2) 0.0588(7) Uani 1 1 d . . . . .
C7 C 0.2047(2) 0.1983(2) 0.5681(2) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.2305(2) 0.0845(2) 0.5324(2) 0.0596(7) Uani 1 1 d . . . . .
C16 C 0.3415(2) 0.3873(2) 0.3828(2) 0.0664(8) Uani 1 1 d . . . . .
H16A H 0.356530 0.360377 0.311471 0.080 Uiso 1 1 calc R U . . .
H16B H 0.331237 0.469173 0.378614 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2293(2) 0.3313(2) 0.4063(2) 0.0656(8) Uani 1 1 d . . . . .
H15A H 0.211662 0.260650 0.364279 0.079 Uiso 1 1 calc R U . . .
H15B H 0.158367 0.380860 0.384956 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2143(3) 0.5083(3) 0.6129(2) 0.0691(8) Uani 1 1 d . . . . .
H14 H 0.269811 0.549178 0.582039 0.083 Uiso 1 1 calc R U . . .
C11 C 0.0453(2) 0.3879(3) 0.7068(2) 0.0719(8) Uani 1 1 d . . . . .
H11 H -0.011170 0.347063 0.736478 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1391(3) 0.5603(3) 0.6737(2) 0.0746(9) Uani 1 1 d . . . . .
C12 C 0.0564(3) 0.5044(3) 0.7208(2) 0.0768(9) Uani 1 1 d . . . . .
H12 H 0.008573 0.543726 0.761359 0.092 Uiso 1 1 calc R U . . .
C6 C 0.3225(3) 0.0611(3) 0.4754(3) 0.0759(8) Uani 1 1 d . . . . .
H6 H 0.371409 0.119999 0.459547 0.091 Uiso 1 1 calc R U . . .
C5 C 0.3421(3) -0.0473(3) 0.4423(3) 0.0831(9) Uani 1 1 d . . . . .
H5 H 0.403896 -0.061176 0.404261 0.100 Uiso 1 1 calc R U . . .
C2 C 0.1610(3) -0.0074(3) 0.5530(3) 0.0809(9) Uani 1 1 d . . . . .
H2 H 0.098953 0.004450 0.591141 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2725(4) -0.1342(3) 0.4646(3) 0.0898(10) Uani 1 1 d . . . . .
H4 H 0.287162 -0.207664 0.442658 0.108 Uiso 1 1 calc R U . . .
C18 C 0.5140(3) 0.3477(3) 0.7415(3) 0.0954(11) Uani 1 1 d . . . . .
H18A H 0.572558 0.392039 0.713413 0.143 Uiso 1 1 calc R U . . .
H18B H 0.554679 0.310672 0.810873 0.143 Uiso 1 1 calc R U . . .
H18C H 0.450475 0.396475 0.755805 0.143 Uiso 1 1 calc R U . . .
C3 C 0.1813(4) -0.1148(3) 0.5187(3) 0.0992(11) Uani 1 1 d . . . . .
H3 H 0.132479 -0.174609 0.532458 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.212(3) . ?
O2 N2 1.384(2) . ?
O2 C18 1.413(3) . ?
N2 C17 1.339(3) . ?
N2 C8 1.447(3) . ?
F1 C13 1.362(3) . ?
N1 C10 1.425(3) . ?
N1 C7 1.284(3) . ?
C17 C16 1.499(4) . ?
C8 C9 1.522(4) . ?
C8 C7 1.531(3) . ?
C8 C15 1.546(3) . ?
C9 C10 1.372(3) . ?
C9 C14 1.358(4) . ?
C10 C11 1.378(4) . ?
C7 C1 1.456(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.388(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C13 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(4) . ?
C13 C12 1.364(4) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.350(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.353(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 C18 112.8(2) . . ?
O2 N2 C8 119.37(18) . . ?
C17 N2 O2 122.82(19) . . ?
C17 N2 C8 117.7(2) . . ?
C7 N1 C10 107.7(2) . . ?
O1 C17 N2 125.2(3) . . ?
O1 C17 C16 129.0(2) . . ?
N2 C17 C16 105.8(2) . . ?
N2 C8 C9 115.1(2) . . ?
N2 C8 C7 115.9(2) . . ?
N2 C8 C15 100.39(18) . . ?
C9 C8 C7 99.9(2) . . ?
C9 C8 C15 112.9(2) . . ?
C7 C8 C15 113.3(2) . . ?
C10 C9 C8 106.6(2) . . ?
C14 C9 C8 131.5(2) . . ?
C14 C9 C10 121.8(3) . . ?
C9 C10 N1 112.3(2) . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 N1 126.3(3) . . ?
N1 C7 C8 113.2(2) . . ?
N1 C7 C1 121.2(2) . . ?
C1 C7 C8 125.5(2) . . ?
C6 C1 C7 123.3(3) . . ?
C2 C1 C7 120.3(3) . . ?
C2 C1 C6 116.4(3) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C17 C16 C15 105.8(2) . . ?
H16A C16 H16B 108.7 . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C8 C15 H15A 110.7 . . ?
C8 C15 H15B 110.7 . . ?
C16 C15 C8 105.4(2) . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C9 C14 H14 122.1 . . ?
C9 C14 C13 115.8(3) . . ?
C13 C14 H14 122.1 . . ?
C10 C11 H11 120.9 . . ?
C10 C11 C12 118.1(3) . . ?
C12 C11 H11 120.9 . . ?
F1 C13 C14 117.8(3) . . ?
F1 C13 C12 117.8(3) . . ?
C12 C13 C14 124.4(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.8 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C16 C15 166.8(3) . . . . ?
O2 N2 C17 O1 -5.3(4) . . . . ?
O2 N2 C17 C16 175.0(2) . . . . ?
O2 N2 C8 C9 76.5(3) . . . . ?
O2 N2 C8 C7 -39.5(3) . . . . ?
O2 N2 C8 C15 -162.0(2) . . . . ?
N2 C17 C16 C15 -13.5(3) . . . . ?
N2 C8 C9 C10 -130.2(2) . . . . ?
N2 C8 C9 C14 53.1(4) . . . . ?
N2 C8 C7 N1 129.5(2) . . . . ?
N2 C8 C7 C1 -53.8(3) . . . . ?
N2 C8 C15 C16 -20.8(3) . . . . ?
F1 C13 C12 C11 179.9(2) . . . . ?
N1 C10 C11 C12 178.2(2) . . . . ?
N1 C7 C1 C6 -175.1(2) . . . . ?
N1 C7 C1 C2 5.9(4) . . . . ?
C17 N2 C8 C9 -107.6(2) . . . . ?
C17 N2 C8 C7 136.3(2) . . . . ?
C17 N2 C8 C15 13.9(3) . . . . ?
C17 C16 C15 C8 21.6(3) . . . . ?
C8 N2 C17 O1 179.0(2) . . . . ?
C8 N2 C17 C16 -0.7(3) . . . . ?
C8 C9 C10 N1 4.4(3) . . . . ?
C8 C9 C10 C11 -175.8(2) . . . . ?
C8 C9 C14 C13 175.8(3) . . . . ?
C8 C7 C1 C6 8.5(4) . . . . ?
C8 C7 C1 C2 -170.5(2) . . . . ?
C9 C8 C7 N1 5.2(3) . . . . ?
C9 C8 C7 C1 -178.2(2) . . . . ?
C9 C8 C15 C16 102.3(2) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C9 C14 C13 F1 179.7(2) . . . . ?
C9 C14 C13 C12 0.1(4) . . . . ?
C10 N1 C7 C8 -2.8(3) . . . . ?
C10 N1 C7 C1 -179.7(2) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C7 N1 C10 C9 -1.1(3) . . . . ?
C7 N1 C10 C11 179.1(3) . . . . ?
C7 C8 C9 C10 -5.4(2) . . . . ?
C7 C8 C9 C14 178.0(3) . . . . ?
C7 C8 C15 C16 -145.1(2) . . . . ?
C7 C1 C6 C5 -179.1(3) . . . . ?
C7 C1 C2 C3 178.7(3) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C15 C8 C9 C10 115.3(2) . . . . ?
C15 C8 C9 C14 -61.4(4) . . . . ?
C15 C8 C7 N1 -115.2(2) . . . . ?
C15 C8 C7 C1 61.5(3) . . . . ?
C14 C9 C10 N1 -178.6(2) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C14 C13 C12 C11 -0.5(5) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C18 O2 N2 C17 79.1(3) . . . . ?
C18 O2 N2 C8 -105.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
